1069-03-0

Basic information

• Product Name: 2-keto-3-deoxyoctonate
• Synonyms: 2-Keto-3-deoxy-D-manno-octonic acid;2-Keto-3-deoxyoctulosonic acid;2-Octulosonic acid, 3-deoxy-;3-Deoxy-2-octulosonic acid;3-Deoxy-alpha-D-manno-2-octulosonic acid;3-Deoxy-D-mannoctulosonate;3-Deoxy-D-mannooctulosonate
• CAS NO: 1069-03-0
• Molecular Formula: C8H14O8
• Molecular Weight: 238.19196
• Product Categories: Pharm intermediate
• Mol File: 1069-03-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 621.7°C at 760 mmHg
• Flash Point: 343.8°C
• Appearance: /
• Density: 1.684g/cm³
• Vapor Pressure: 4.64E-18mmHg at 25°C
• Refractive Index: 1.597
• CAS DataBase Reference: 2-keto-3-deoxyoctonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-keto-3-deoxyoctonate(1069-03-0)
• EPA Substance Registry System: 2-keto-3-deoxyoctonate(1069-03-0)

Safety Data

• Hazardous Substances Data: 1069-03-0(Hazardous Substances Data)

Usage

General Description

2-keto-3-deoxyoctonate, also known as KDO, is a key intermediate in the biosynthesis of bacterial lipopolysaccharides, essential components of the cell envelope of Gram-negative bacteria. It is a seven-carbon sugar derivative that plays a crucial role in the formation of the outer membrane and is involved in the recognition of pathogenic bacteria by the host immune system. KDO is also an important target for the development of antimicrobial agents and vaccines, as its unique structure makes it a potential candidate for interfering with bacterial cell envelope biosynthesis and immune recognition. Overall, KDO is a critical component in the biology of Gram-negative bacteria and a potential target for therapeutic interventions against bacterial infections.

InChI:InChI=1/C8H14O8/c9-2-5(12)7(14)6(13)3(10)1-4(11)8(15)16/h3,5-7,9-10,12-14H,1-2H2,(H,15,16)

Upstream product

• 113409-52-2 3-deoxy-2,5,6,7,8-penta-O-acetyl-L-gulo-2-octenoic acid γ-lactone 
• 113443-91-7 2-hydroxy-3-deoxy-5,6,7,8-tetra-O-acetyl-L-gulo-2-octenoic acid γ-lactone 
• 328-42-7 Oxalacetic acid 
• 609-06-3 L-xylose 

Related news

Quantification of 2-keto-3-deoxyoctonate (cas 1069-03-0) in (lipo)polysaccharides by methanolytic release, trifluoroacetylation and capillary gas chromatography08/01/2019

Several conditions of acidic anhydrous methanolysis were examined to optimize the release and minimize the degradation of unphosphorylated 2-keto-3-deoxy-d-manno-octonic acid (KDO) from bacterial lipopolysaccharides and polysaccharides. The reaction was monitored by capillary gas chromatography ...detailed

Quantification of Bacterial Lipopolysaccharides by the Purpald Assay: Measuring Formaldehyde Generated from 2-keto-3-deoxyoctonate (cas 1069-03-0) and Heptose at the Inner Core by Periodate Oxidation07/31/2019

We have adapted the purpald assay (M. S. Quesenberry and Y. C. Lee,Anal. Biochem.234, 50–55, 1996) to quantify lipopolysaccharide (LPS) content in solution in 96-well microtiter plates at room temperature. This method employs the oxidation of unsubstituted terminal vicinal glycol groups in 2-ke...detailed

Lipopolysaccharide-binding lectin from the horseshoe crab, Limulus polyphemus, with specificity for 2-keto-3-deoxyoctonate (cas 1069-03-0) (KDO)07/30/2019

A lipopolysaccharide (LPS)-binding lectin was recovered from the serum of Limulus polyphemus by ion-exchange chromatography. Electrophoretic analysis of this lectin preparation revealed three poorly migrating bands. When whole serum was incubated with glycolipid obtained from the Rc mutant of Sa...detailed

A new and improved microassay to determine 2-keto-3-deoxyoctonate (cas 1069-03-0) in lipopolysaccharide of gram-negative bacteria07/29/2019

A procedure is described to determine 2-keto-3-deoxyoctonate (KDO) present in lipopolysaccharide (LPS) of gram-negative bacteria. The method involves the treatment of LPS with 0.2 n H2SO4 at 100°C for 30 min to release KDO, followed by its reaction with periodic acid, sodium arsenite, and thiob...detailed

Occurrence of O-phosphorylated 2-keto-3-deoxyoctonate (cas 1069-03-0) in the lipopolysaccharide of Bacteroides gingivalis07/28/2019

Periodate-thiobarbituric acid reaction-positive substances were found in the strong acid hydrolysates of the lipopolysaccharide (LPS) from Bacteroides gingivalis 381. They were not identical to 2-keto-3-deoxyoctonate (KDO) in high-voltage paper electrophoresis (HVPE), their electrophoretic mobil...detailed

Analysis of the 2-keto-3-deoxyoctonate (cas 1069-03-0) (KDO) region of lipopolysaccharides isolated from non-01 Vibrio cholerae 05R07/27/2019

Phosphorylated 2-keto-deoxyoctonate (KDO) has been detected in the stronga-acid hydrolysates of lipopolysaccharides (LPS) of family Vibroonaceae including Vibrio cholerae. Structural analysis of LPS isolated from a rough mutant of non-01 V. cholerae 05 by dephosphorylation, periodate oxidation a...detailed

Detection of 2-keto-3-deoxyoctonate (cas 1069-03-0) in endotoxins isolated from six reference strains of the Bacteroides fragilis group07/26/2019

1.1. Endotoxins isolated from six serotype specific reference strains of the Bacteroides fragilis group were dephosphorylated by treatment with aqueous 50% hydrofluoric acid.2.2. Mild acidic hydrolysis of the dephosphorylated endotoxins released 2-keto-3-deoxyaldonic acid, the presence of which ...detailed

Chemical structure of the 2-keto-3-deoxyoctonate (cas 1069-03-0) region of lipopolysaccharide isolated from Porphyromonas (Bacteroides) gingivalis07/24/2019

Structural analysis of the 2-keto-3-deoxyoctonate region of lipopolysaccharide (LPS) isolated from Porphyromonas (Bacteroides) gingivalis was carried out. The substitution of the polysaccharide portion on the KDO was determined by gas chromatography/mass spectrometry of the product obtained by s...detailed

Relevant articles and documents

Structural diversity of Burkholderia pseudomallei lipopolysaccharides affects innate immune signaling

Burkholderia pseudomallei (Bp) causes the disease melioidosis. The main cause of mortality in this disease is septic shock triggered by the host responding to lipopolysaccharide (LPS) components of the Gram-negative outer membrane. Bp LPS is thought to be a weak inducer of the host immune system. LPS from several strains of Bp were purified and their ability to induce the inflammatory mediators TNF-α and iNOS in murine macrophages at low concentrations was investigated. Innate and adaptive immunity qPCR arrays were used to profile expression patterns of 84 gene targets in response to the different LPS types. Additional qPCR validation confirmed large differences in macrophage response. LPS from a high-virulence serotype B strain 576a and a virulent rough central nervous system tropic strain MSHR435 greatly induced the innate immune response indicating that the immunopathogenesis of these strains is different than in infections with strains similar to the prototype strain 1026b. The accumulation of autophagic vesicles was also increased in macrophages challenged with highly immunogenic Bp LPS. Gene induction and concomitant cytokine secretion profiles of human PBMCs in response to the various LPS were also investigated. MALDI-TOF/TOF was used to probe the lipid A portions of the LPS, indicating substantial structural differences that likely play a role in host response to LPS. These findings add to the evolving knowledge of host-response to bacterial LPS, which can be used to better understand septic shock in melioidosis patients and in the rational design of vaccines.

CONVERSION OF CYCLIC AND ACYCLIC THIOACETALS OF SUGARS INTO 2-KETO-3-DEOXY-L-gulo-OCTONIC ACID

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